Mock Test 3 (Organic Chemistry) +2

Transcription

1 Mock Test (rganic hemistry) +2 Section (Single nswer) 1. Benzene is allowed to react with succinic anhydride in the presence of anhydrous ll and subsequently treated with dilute l. The product formed is a. c. d. (i) 25Na / In the given reaction 25 ( 2 ) 2 25 [X] ; 2 5 a. c. d. [X] is:. With respect to its reactivity towards hydride reducing agents, an aldehyde is a. more reactive than an ester because electron donation by oxygen makes the carbonyl group of the ester less electron deficient. less reactive than an ester because electron withdrawn by oxygen makes the carbonyl group of the ester more electron deficient. c. less reactive than an ester because electron donation by oxygen makes the carbonyl group of the ester less electron deficient. d. more reactive than an ester because electron withdrawn by oxygen makes the carbonyl group of the ester more electron deficient. 4. The IUP name of the compound shown here is: a. 4-keto-5-n-propylheptanoic acid 2-carboxyethyl--hexyl ketone c. -(-hexylcarbonyl)propanoic acid d. 5-ethyl-4-ketooctanoic acid 5. Each of the following two ketones is treated with a catalytic amount of base (K) ( ) P1 ( ; ) P ; 2 Which of the following statement is true regarding above reactions a. Both P 1 as well as P 2 are racemic mixture Both P 1 as well as P 2 are optically pure enantiomers c. P 1 is optically pure while P 2 is a racemic mixture d. P 1 is a racemic mixture while P 2 is optically pure r. Sangeeta Khanna Ph. 1 EMISTRY ING IRLE G:\+ 2 MK TEST - (Non-Medical).doc 5

2 Sol. Enolisation is possible in Ist but not in IInd case. 6. ldol ondensation proceeds by carbon-carbon bond formation between an enolate donor and a carbonyle acceptor. For each of the following aldol products ( to E) select a donor and an acceptor compound from the list at the bottom of the page (compounds through ). Find the correct match in the given combination ldol Product List I. B... ( ) 2 () 2 E List II = B E B E a ,2 7,6 4,5 1,2 7 2,6 c. 4,8 8,5 7 2,6 d. 7,6 1,2 7 8,6 B Section B (More than ne nswer) 7. Which of the following reacts with Na giving 2? a. c. d. Picric acid, B,, 8. ozonolysis dil B xidation ollin s Reagent Na/I 2 + E(ppt) a. can be open chain structure while E is a close ring structure is 6-Ketoheptanal c. is d. is r. Sangeeta Khanna Ph. 2 EMISTRY ING IRLE G:\+ 2 MK TEST - (Non-Medical).doc

3 Sol. B & = ; B = ; = ; = ; E = I 9. Which are correctly matched a. I SN 1 + B (cidic to litmus) 2 = I SN 2 + B [Both & B give iodoform test] c I SN 2 + B [neutral for litmus but give iodoform test] d I SN 2 + B [Both are acidic for litmus test],b, 10. optically active alcohol 9 18 on dehydration with l 2 produces B( 9 16 ) which exists in two stereoisomeric forms. For ozonolysis of B followed by work up with Zn 2 produces and ( 7 12 ). on treatment will Lil 4 produces ( 7 14 ). on dehydration produced. Identify the correct answers. a. is 2 2 is c. d. B, is 2 is Sol. 11. Which of the following are not resolvable? Sol. a. () 2 (B) a. 2,-Pentadiene c. d., 5 Me N = () = () N N N (llenes of this type show optical activity) Me r. Sangeeta Khanna Ph. EMISTRY ING IRLE G:\+ 2 MK TEST - (Non-Medical).doc

4 The cis form shows optical activity c. The trans form does not show optical activity due to the centre of symmetry. d. oes not show optical activity due to centre of symmetry. SETIN (omprehension Type) omprehension 1 arbon-oxygen double bond are easily reduced by NaB 4 or Lil 4. The actual reducing agent in these reduction is hydride ion ( ). - Θ Θ The metal-hydrogen bond in Lil 4 is more polar than metal-hydrogen bond in NaB 4. s a result Lil 4 is strong reducing agent than NaB 4. Esters, carboxylic acids, amides cannot be reduced by NaB 4. The carbonyl group of amide reduced to methylene group by Lil Find the correct product of the following reaction: N 2 Lil 4 a. 2 N 2 N 2 c. d. No Reaction N 2 NaB ' X' ;Identify X : a. c. d. B Lil ' Y' ; Identify Y : 2 a r. Sangeeta Khanna Ph. 4 EMISTRY ING IRLE G:\+ 2 MK TEST - (Non-Medical).doc c. 2 d. 2

5 omprehension 2 NNIZZR RETIN: (disproportionation or self oxidation Reduction) Θ Θ Θ Θ = Θ + Θ + Θ Which of the following is a product (s) of following reaction? + +? a. + c. + d = + - annizaro X Y ; X and Y are (acid) (alcohol ) RXn + + a.,, 2 c. ; d. None of these 17. Predict the product of the annizzaro reaction of the following compound: onc. Na 2 a. Na Na 2 Na c. 2 d. 2 Na Sol. The group which is p to electron withdrawing group (i.e., ) gets oxidized while the m group gets reduced. = = Na (Intramolecular annizzaro reaction) Θ Na + Na 2 2 r. Sangeeta Khanna Ph. 5 EMISTRY ING IRLE G:\+ 2 MK TEST - (Non-Medical).doc

6 SETIN (MTRIX MT) This Section contains questions. Each question has four choices (, B, and ) given in olumn I and five statements (p, q, r, and s) in olumn II. No negative Marking (8 = 24 Marks) 18. Match the following: olumn I olumn II Ph () / Ph 2 (p) arbocation Ph (B) /2 Ph (q) Transition state () /2 (r) lkyl oxygen bond cleavage () /2 (s) cyl oxygen bond cleavage Sol. () p, r; (B) p, s; () p, r; () q, r 19. Match the olumn I with olumn II. olumn I olumn II ()? 2 (p) Zn(g) + l l l (B) (q) N 2 N 2 + glycol R 2 () (r) L/ 2 () (s) Red P + I Sol. q, B p, s; r; s r. Sangeeta Khanna Ph. 6 EMISTRY ING IRLE G:\+ 2 MK TEST - (Non-Medical).doc

7 Section E (Integer Type) 20. ow many of the following functional groups are reduced by NaB 4. (i) amine (ii) cyanide (iii) ester (iv) acid (v) aldehyde (vi) ketone (vii) alkene (viii) cid halide (ix) anhydride (x) tert. halide Sol. 6; cyanide, aldehyde, ketone, acid halide, anhydride, tert. halide 21. Reaction of glycerine with ethanal will give total X number of products [including stereoisomer] The number X is Sol Trans/cis cis (d & ) Trans (d & ) 22. on intermolecular esterification will give. ow many products [including stereoisomer] Sol. cis (d, ) Trans (meso) 2. Number of chiral centre in the given compound are Sol ow many Grignard molecule will be required for complete reaction of the given compound. Sol. 4 l r. Sangeeta Khanna Ph. 7 EMISTRY ING IRLE G:\+ 2 MK TEST - (Non-Medical).doc